QD164 : Synthesis of new derivatives of imidazo[1,2-a] pyridines by Pd-Cu catalyst
Thesis > Central Library of Shahrood University > Chemistry > MSc > 2007
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Abstarct: In this work facile synthesis of new derivatives of imidazo[1,2-a]pyridines through palladium-catalyzed heteroannulation is reported.
Treatment of 2-aminopyridine (1) with propargyl bromide in refluxing acetonitrile affords 2-amino-1-(2-propynyl) pyridinium bromide (107) in good yield.
When compound (107) in DMF was reacted with aryl iodides (108a-i) and triethylamine in the presence of bis(triphenylphosphine)palladium chloride(II) and cuprous iodide at room temperature, 2-substituted imidazo[1,2-a] pyridines (109a-i) were obtained in high yields. The reactions were carried out under an argon atmosphere, and the DMF and triethylamine mixture was degassed prior to use.
Also compound (107) was treated in DMF with the aryl halides (108a-i) and triethylamine in the presence of [PS-En-Pd(II)], triphenylphosphine and copper iodide at room temperature, the 2-substituted imidazo[1,2-a]pyridines (109a-i) were obtained in good to high yields. The advantages of our heterogeneous catalytic [PS-En-Pd(II)] system over others are Excellent performance and reusability of the catalyst.
In conclusion the described method for the synthesis of imidazoheterocycles is an easy and one-pot procedure with good to high yields.
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Keeping place: Central Library of Shahrood University
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Keeping place: Central Library of Shahrood University
Visitor: